3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 67323523, compound

HRID 1397446Notes

Reaction equation

HRID 1397446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3([CH2:20][NH2:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[S:12][CH:13]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[F:22][C:23]([F:39])([F:38])[C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[N:25]=1>>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3([CH2:20][NH:21][C:32](=[O:33])[C:31]4[CH:35]=[CH:36][CH:37]=[C:29]([C:26]5[N:25]=[C:24]([C:23]([F:39])([F:38])[F:22])[O:28][N:27]=5)[CH:30]=4)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[S:12][CH:13]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324369HCID 67324369, compound

Product 1

HCID 67323523HCID 67323523, compoundYield 10%

Procedure

This compound was synthesized from (4-(4-(3,5-difluorophenyl)thiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (20 mg, 10% yield). 1H NMR (300 MHz, CDCl3) δ 8.45 (s, 1H), 8.24 (d, J=8.3 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 7.64-7.54 (m, 2H), 7.35 (d, J=5.5 Hz, 1H), 6.73 (m, 2H), 3.95 (m, 2H), 3.85 (d, J=5.5 Hz, 2H), 3.70 (m, 2H), 2.28 (m, 2H), 2.05 (m, 2H). MS (ESI) m/z: Calculated for C25H19F5N4O3S: 550.11. found: 551.1 (M+H)+.

Sources & evidence

ORD record
ord-c0cfb9e5bb70496ca3fd41435b698bb9
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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